Fall Events in Sarasota: This Season’s Must-See Moments

Autumn is an exciting time to visit and be in Sarasota County. With the temperatures cooling and the changing of leaves (just kidding, we have palm trees), there are an abundance of festive local events that blend sunshine, community and creativity into one extraordinary season.

From sandcastle competitions, 3D chalk artistry and a medieval-themed fair to spooky Halloween trails, Oktoberfests and Pride block parties, there are more reasons that not to make a trip to Sarasota County this fall season!

Performing Arts Events

Sarasota Contemporary Dance Performers

Kick off the beginning of the performing arts season in September with Sarasota County’s rich new lineup of upcoming shows and performances across Florida’s Cultural Coast®. From theater and dance to live concerts, opera, stand-up comedy and more, fall brings fresh experiences that showcase the area’s creative spirit.

Sarasota ROCKtoberfest

Fall means it’s time for ROCKtoberfest at JD Hamel Park along Sarasota's Bayfront! Celebrate this beloved German tradition with lively music, mouthwatering food, big pints of beer, shopping, family and fun. This annual 3-day Oktoberfest experience is coupled with fantastic live music performances and local food and arts vendors. Best part is, admission is free to come rock and roll!

Sarasota Water Lantern Festival

Nathan Benderson Park Lake

The breathtaking Water Lantern Festival is an amazing experience where you'll witness the magic of the lanterns as they light up the water at Nathan Benderson Park. Held each October on the lake of a 600-acre community park, get your tickets early to this family-friendly and anticipated event. After the show, head over to the neighboring PopStroke for a round of putt-putt golf under the lights, or check out one of the many University Town Center's restaurants, bars and lounges for dinner. 

Downtown Sarasota Craft Festival

This popular craft festival draws crowds to Downtown Sarasota each October. Crafters and artisans showcase handmade jewelry, pottery, ceramics, photography, paintings, clothing and more. The on-site Green Market is an added bonus for plant lovers, featuring orchids and other tropical plants, plus handmade soaps, gourmet spices and fresh kettle corn.

Gulfcoast Pride Festival & Street Party

An ever-growing LGBTQ destination for locals and visitors, Sarasota County will be bustling with rainbow colors for fall at the Gulfcoast Pride Festival in the Rosemary District of Downtown Sarasota. This vibrant, inclusive celebration of the LGBTQ community will feature more than 100 vendors with pride-themed goods and swag, performances by local and national entertainers and plenty of street food from local restaurants and artisans.

Lights at Spooky Point

Pioneer Cemetery and the White Cottage at the Historic Spanish Point

The gardens at Selby’s Historic Spanish Point campus in Osprey transform into an eerie yet enchanting glow-in-the-dark spectacle each October. This Halloween walk-thru light show runs for most of the month, offering family-friendly frights and haunting sights. Get your tickets and come early to explore the enchanting grounds by daylight, then stay after dark to see the gardens in a whole new light. 

Repticon Sarasota

Calling all reptile enthusiasts—Repticon Sarasota brings the world of exotic animals to town at the end of October. Browse vendors offering reptiles and other popular pets along with supplies, feeders, enclosures and reptile-themed merchandise. This family-friendly expo is equal parts exciting and educational, making it a must for animal lovers and collectors of all ages. 

Siesta Key Crystal Classic

Sand sculpture artist on Siesta Key Beach

Fun on the beach isn’t just for summer. Each November, Siesta Beach draws crowds as sand sculptors from around the world create massive works of art at the annual Siesta Key Crystal Classic. This four-day event showcases both solo artists and teams carving large-scale masterpieces. Beachgoers can join workshops, enjoy live music, browse and shop the Vendor Village of retail and food, or even compete in an amateur contest. For tips on making the most of your visit, check out a weekend itinerary for the festival.

International Chalk Festival

Chalk Festival Artist

Each fall, Sarasota’s Historic Burns Square transforms into an open-air gallery during the Chalk Festival, the largest gathering of 3-D illusion artists and pavement artists in the world. Since 2007, the festival has welcomed more than 150 artists from over 30 countries to turn our city sidewalks and streets into dazzling masterpieces. Over the course of three days, visitors can stroll the downtown district and watch these modern-day masters at work, bringing an ancient art form to vibrant life before their eyes. Each year's event brings a new lineup of food trucks, live music, vendors and interactive areas for the kids to enjoy. 

Wellen Park Wine Festival

Continuing in November, raise your glass at the annual Wellen Park Wine Festival in Downtown Wellen Park. This lakeside celebration is anything but stuffy—featuring nearly 40 distinguished vintners, small bites from local restauranteurs, live jazz on stage at the amphitheater. The ticketed 21 and older event will also have exclusive offerings like a VIP dinner, Wine Tasting 101 class and early-access tasting sessions for one weekend of stellar wine and community.

Sarasota Medieval Fair

Knights on horseback at the Sarasota Medieval Fair

Step into a world where history and pageantry collide at the Sarasota Medieval Fair, set amid nearly 50 acres of majestic oaks at the Woods of Mallaranny in Myakka City. Each weekend in November, the county comes alive with full-contact jousts, human chess matches, jesters, belly dancers and roaming minstrels. Indulge in turkey legs and ales, explore artisanal wares and delight the kids with rides and the Children’s Realm. With feasts, tournaments and medieval merriment on every corner, it’s a boldly immersive experience—and a favorite fall tradition for families of all ages. 

Downtown Venice Art Festival

Hosted by the same organization that puts on Sarasota's Art Festival, in November it’s Historic Downtown Venice’s turn to fill the streets with 100 of the nation’s most notable artists. The annual weekend festival showcases handcrafted work across many mediums including photography, jewelry, paintings, sculpture, ceramics, glass, mixed media and more.

Architecture Sarasota MOD Weekend

Fans of mid-century modern architecture and décor will definitely want to check out this annual celebration of this style its influence on the local landscape that takes place over a weekend in November. Consisting of kayak, trolley and walking tours, parties and more, it aims to celebrate the contributions of renowned architects who helped foster Sarasota’s MCM design movement and, ultimately, the Sarasota School of Architecture. Learn more about Sarasota Mod Weekend. Prices and locations vary by event.